


The Journey of a Professor

by 464kiki



Category: Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Accurate (as best I can) depictions of the Pokémon world, All characters are 18+ unless specified by canon or author, Dorks, Eventual Romance, F/M, Falling In Love, Fluff and Angst, Love Triangles, Other Additional Tags to Be Added, Rating May Change, Slow Burn, Tags May Change
Language: English
Status: In-Progress
Published: 2020-01-28
Updated: 2020-03-25
Packaged: 2021-02-27 09:00:18
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 14,383
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22454569
Author URL: https://archiveofourown.org/users/464kiki/pseuds/464kiki
Summary: Sakura's childhood dream was to become a Pokemon professor and research how to help improve the bonds between people and Pokemon. However, her startup has been a lot slower than she expected, especially compared to her friend Sonia. Even her friend Leon was able to be so successful at just ten years old. Since no one had endorsed her to do the Gym Challenge, it was difficult to get her foot in the door to her ambitions. However, her luck was about to change when the Champion decided to get nosy with her business.
Relationships: Dande | Leon/Original Female Character(s), Kibana | Raihan/Original Female Character(s)
Comments: 10
Kudos: 52





	1. A Professor’s Proposal

“Umbre-Umbre!” Sakura’s Pokémon Umbreon welcomed as she stepped through the front door of her house. She gave her pet, dubbed Midnight, a small smile, and scratched between her pointed ears. “Thanks for the welcome home, girl.” She spoke softly, giving a pat on Midnight’s slick head and putting her workbag down on the end table beside the door.

Just a typical workday at the Pokémon Center; well, maybe a bit busier than usual. There was that farmer who had three sick Wooloos. It was a smart move on the farmer to bring them in before the sickness spread. Other than that, there wasn’t much new activity at the center. Since the Gym Challenge was going to be coming up, a couple of ten-year-old kids came in to make sure their ‘mon was in tiptop shape before battling one another.

A relaxed sigh escaped Sakura’s lips as she placed her sneakers near the door and coat on the coat rack. Midnight pawed at Sakura’s leg and hopped to the side, signaling she was hungry. Sakura chuckled at the adorable habit she picked up and replied, “Yes, yes, I know you’re hungry. I’ve got to make the food first, though!” She then headed towards the kitchen and began preparing some spicy sausage curry. Putting a couple of Cheri berries along with some Tamato and Occa berries, the sausages and curry mix into a pot, she began stirring the mixture together. Midnight was already prancing around Sakura’s feet in eagerness until there was a knock on the door.

“Hold on, I’ll be there in a minute!” Sakura yelled at the door, hoping it was heard by whoever was waiting. Quickly finishing up Midnight’s meal and setting it down on the floor in a bowl, Sakura rushed to the door to unlock it. Low and behold, it was the familiar, purple-haired champion of the Galar region, Leon. It was a good thing Sakura recognized the purple hair too because she was soon enveloped in a death grip of a hug by her childhood friend.

“Guess who’s back in town for a bit?” Leon exclaimed, lifting his short friend in the air. With a struggled wheeze, Sakura responded, “I think a Bewear got loose in Postwick and plans to wreak havoc in my house!” He emitted a hearty laugh and set her back on the ground. Heaving for some air, she also delivered a short wave to Leon’s Charizard, watching the greeting from behind. However, realizing more than one minute has passed since she hailed Leon, she shot straight up and stepped to the side, hurriedly rambling, “Oh crap! You’ve been standing outside in the sun for way too long! I’m sorry! Please come inside. Charizard can play in the backyard, and I’m sure Midnight will join him after dinner.” Leon raised an eyebrow and gave a light chuckle as he stepped inside. “Sakura, you do know that the sun has already set over the hills, right?” Sakura’s cheeks turned a pale pink as she swiftly closed the door after him. “Y-Yeah, totally! I-I was just messing with you! Yeah!” She was glad his back was to her so she could mask her embarrassment.

Clearing her throat, she moved in front of him, hoping her blush had gone away. “Anyway, would you like something to eat? I’m sure your journey back home was pretty long. Especially with how lost you can get.” She teased, already scurrying to the kitchen to fix something at Leon’s request. Sakura almost tripped on Midnight as she rushed out the doggy door to likely roughhouse with Charizard. “I’m good, thank you. I ate along the way and had a couple of snacks at mom’s house. Some water is fine, though, since you left me drying up in the hot sun.” Leon joked back as he sat on the couch and placed his cap on the coffee table. Sakura conveyed a nervous glare through the wall dividing the living room and kitchen at him while pouring some cold water into two glasses.

Leisurely walking to the living room, Sakura placed the glasses down on coasters and took her spot across the couch from Leon. “So, what brings you to my home? This doesn’t seem like this is just a brief visit.” She started, relaxing against the cushions. Leon shifted his body to face hers before speaking. “Well, there was something I wanted to talk to you about that I think you might like.” He flashed a smile before continuing. “I was wondering if you’d like to go see the last exhibition match before the Gym Challenge starts this year.” He paused to hear a reaction from Sakura, already predicting what she would say. “Oh, that does sound nice, Leon, but I don’t think I can. I’ve got work on Friday and Saturday, so the journey all the way to Wyndon Stadium would be too long.” Sakura looked down in shame for having to turn down the offer but then shot up, wide-eyed when Leon said, “Actually, I talked to your boss about it already. She seemed excited to see you take a break from work and immediately allowed the time off. Paid even!”

Sakura couldn’t believe what she heard. Well, she could, her boss loved her as a hard-working employee who cared deeply about the health of the Pokémon patients. But, she didn’t expect Leon to directly speak to her without telling her first. She deemed this must, too, have a catch or mean a lot to him. “I…” she stopped for a moment, thinking of her words carefully before proceeding, “Thank you for the offer, but are you sure you want to give that ticket to me? I think Hop would enjoy seeing you live and deserves them more than I do.” Leon frowned and crossed his arms. “Of course, I want to give you the ticket, it’s a VIP front row spot, where the gym leaders sit.” Her jaw dropped to the floor. She stuttered out in return, “W-WHAT?! L-Leon! That’s way too much! That had to cost a fortune! I would stick out like a sore thumb among the gym leaders! Please give it to Hop, he would appreciate it way more than I could. I’d just be an embarrassing mess and-” Sakura was cut off by a hand being placed on her knee. Leon extended a patient smile and reassured, “Sakura, you’ll be fine. Hop’s already had a seat by the gym leaders before multiple times. You’ve only seen the matches on TV or your phone. The gym leaders are all nice people. You will be fine. You can bring Midnight as well since she’s small enough.”

She had run out of excuses other than anxiety-ridden ones. She avoided his gaze as she tried to calm her nerves. “Would…would it be ok with the gym leaders? O-Or, would you be there?” Another smile, but brighter, graced his face. “They would totally be fine with you being there. If you want, I’ll ask just to appease you, but they deal with strangers on the daily. It would be no different than a fan. And, of course, I would be there! I’m one of the people battling.” His smile turned into a mischievous grin. “Pluuuus, you could bring your journal and analyze the battle.” Right in the weak spot. He knew that her weakness was analyzing just about anything that interest her. Since Sakura’s dream is to be a professor like her friend Sonia, she had taken most opportunities to watch any Pokémon battle she could; typically, the live ones she recorded for future viewing. She forgot that it would be one of the benefits of going.

“Plus, we’ll travel together to Wyndon Stadium.” Leon hesitated for a moment, asking, “As long as that’s alright with you?” Another blush snuck up on Sakura’s face as she nodded swiftly. “Y-Yeah! That’s, of course, fine by me! That’ll allow Charizard and Midnight to spend more time together.” A light blush also snuck up on Leon’s face as well, along with an awkward smile. “Great, then, I should be heading back out. Mom wants me to spend the night at home. I’ll see you Thursday after work, then?” He stood up from his seating, placing his cap back on, and gulped down the now room temperature water. “Yup! I’ll be waiting out front of the Pokémon Center.” Sakura replied, taking the empty glass from Leon. “It’s a date then!” Both got taken back from what Leon said without thinking, and he hastily said, “Well gotta go, I’ll see myself out. You have a nice night, see you later!” Leon rushed out the door, but closing it carefully, and called Charizard to venture home.

**Notes for the Chapter:**

> Well, hope you all liked the first chapter. I'll release the next chapter sometime this week. It's already written, but I still would like spacing between chapters. Currently working on the third chapter and am about halfway through. This is also my first time posting my work somewhere, so if you guys have any tips on how to use this site, I'd love to hear them!  
> I was also inspired by chaoticlogic's fanfic, Stumbling to try and write my own fanfic. There are occasional similarities in broad plot, since their's also an adventure, but I hope I've distinguished it enough to make it stand out on it's own. Definitely check out their story though! Here's the URL for it: https://archiveofourown.org/works/21482878/chapters/51199024


	2. A Champion’s Challenge

Leon couldn’t fathom why he had said, “it’s a date” to Sakura. He prayed that she wouldn’t take it that way and just view it as absentminded words. She probably would, though, since she was oblivious to most romantic advances. Charizard grumbled low in confusion at his owner’s agitated demeanor. Leon glanced over and pat his friend’s head. “I’m fine, buddy. No need to worry.” Leon then began his short stroll back home, contemplating how he’d talk with the gym leaders about their potential guest at the exhibition match and dinner.

Stepping through his mom’s front door, Leon gave his mom a brisk hello from the entrance and climbed upstairs to his bedroom. Hop’s door was closed, but he could overhear him chatting with his Wooloo. He certainly loved his Wooloo. Deciding not to bother them, Leon went inside his room and closed the door behind him. “Eight o’clock, huh? I think everyone should still be awake.” He mumbled to himself as he glimpsed at the clock. Stripping himself down of his shoes, cape, and cap, he plopped into bed and pulled out his Rotom Phone. He opened the group chat that Raihan had put together that included all the gym leaders.

**_Leon_** ** _:_** Hey everyone up? I’ve got a question to ask you all.

**_Raihan_** : Always up. Whatcha need Champ?

**_Piers_** : What’s up?

**_Nessa_** : I’m up dear.

**_Milo_** : Howdy Leon! What’s the question?

A couple of minutes later, the rest of the gym leaders responded.

**_Leon_** : So, you know the VIP ticket I got from the chairman? I didn’t give it to Hop, but instead an old friend of mine. I’m trying to convince her to join the Gym Challenge and will surprise her with an endorsement later at night after the Gym Leader Banquet. She’s a bit shy and wanted me to make sure it would be alright with you all that she’s with us.

Some more minutes passed until Leon received all the expected responses.

**_Piers_** : Doesn’t matter to me, won’t be showing up either way

**_Milo_** : Piers you really shouldn’t keep skipping the exhibition matches.

**_Melony_** : I would be delighted to meet your friend! She’ll definitely be welcomed to sit with us!

**_Allister_** : She’s fine…what kind of Pokémon does she have…?

**_Milo_** : Yeah! She’ be given a warm welcome from me!

**_Opal_** : Does she like Fairy types?

**_Kabu_** : Is she originally from Galar?

**_Nessa_** : OF COURSE she can join us! She was given the ticket after all, no need to ask us.

**_Raihan_** : Is this friend actually your girlfriend? 😏

Leon blushed at Raihan’s comment and speedily replied before anyone got the wrong idea.

**_Leon_** : No! She’s just a childhood friend. You all will get to meet her Friday, so you can ask her your questions.

**_Raihan_** : Ah, so she’s free game then right?

**_Nessa_** : Rai you’ll make her feel uncomfortable. How will we convince her to join the Gym Challenge if you chase her away with your ego? 😂

**_Piers_** : Or bore her with your obsession with weather.

**_Raihan_** : Why must you bully innocent little me? 😔

Leon let the conversation drift to other parts and put his phone on his dresser. He knew that everyone would be alright with Sakura joining already, but still desired to keep his word and ask. He hoped that Raihan wouldn’t cause distress for Sakura, or worse flirt with her, but he at least wouldn’t have to fret about that occurring during the exhibition match; since it was him versus Raihan. Nessa and Melony would also presumably aid in keeping him at bay. Milo too, as long as Nessa isn’t so focused on declaring her rivalry for him. Leon would have to bear in mind to make sure Sakura doesn’t wear any pink clothes or accessories, or else Opal will be doting on her. 

He thought over his plan on how to make the exhibition match and prior journey to Wyndon Stadium an enjoyable experience for Sakura. Opening the top right drawer of his dresser, he pulled out a planner journal and double-checked he acquired all the necessary tickets and passes needed. Train tickets to-and-fro from Wyndon Station, VIP ticket and badge for Sakura, Rondelands hotel keys for him and her, dinner reservations for him and the gym leaders, two letters of endorsement, it all seemed to be accounted for. He was grateful that he asked Chairman Rose about how endorsements work and that he had the power to give them out. He intentionally wanted to give one to Hop as soon as he was old enough to participate, but now that he had to persuade Sakura to join as well, the letter wouldn’t be sufficient.

Putting the items back in the journal and away in their drawer, he laid back down against his pillow and shut his eyes. He pondered about what he would do while idling for Sakura to get off work. Training? Nah, he shouldn’t do that while he’s at home, even if the match is just two days away. Plus, the battle court in the front yard is not large enough for his team. Maybe he could fill time with Hop? He’d be in Trainers’ School till three, though, and he’d have to get ready by five. Leon eventually gave up on his endeavor and ruled it would be better to wing it in the morning. After getting a bit cozier in his bed, he finally drifted into a restless slumber.

_Leon found himself standing up after sitting on the ground. His body ached a little, making him presume he was pushed down. The wind was howling and whirling around his frame, and the sky was dark shades of purple and fuchsia circling a central force. Floating in front of him was a massive Pokémon; its shape resembling that of a skeletal dragon. Some flames brushed passed him, its origin coming from Charizard as he was attacking the gigantic creature. It didn’t react in more than annoyance as it flung it’s three-pronged arm at Charizard, knocking him to the ground. Leon tried to dash towards his fallen partner, but the wind slowed his progress significantly. Another gust flew his way, along with an ear-shattering roar from the beast. Turning his head towards it, he only faced a mouth with pointed teeth chomping his body into two._

**Notes for the Chapter:**

> Seeing two kudos on the first chapter got me too excited to post the next one. I'm sorry if it's a bit short, but I hope it's still enjoyed nonetheless! Still working on the third chapter. Hopefully that will be able to come out this week and be a long one!


	3. A Professor’s Excursion

“My, my, you can’t stop looking at that clock today.” Sakura’s boss, Nancy, spoke from behind, causing Sakura to jump and almost drop the medicine she was going to give to a Rookidee. “Oh! I’m sorry, dearie didn’t mean to startle you.” Sakura glanced behind her a gave a quick smile to her boss before pouring the liquid into a small bowl and presenting it to the Pokémon. “You’re fine, ma’am. I just didn’t expect you. And, as for the clock, I guess I have been keeping my eye on it.” Nancy chuckled and questioned, “I bet you’re excited to go on a date with your boyfriend, hmm?” Sakura’s face flushed, and she swiftly retorted, “W-We’re not dating! Leon is just a childhood friend. You know this, boss!” “Well, he’s certainly taking his sweet time to ask you out.” Sakura gave a sad sigh and put the medicine back on its shelf. “I’m not expecting him to ask me out, boss. He probably has loads of other girls to pick from, and most likely wants to stay friends.” Nancy scoffed at this statement and replied, “But you’re the one he’s known the longest.” She patted Sakura’s shoulder and ambled back to her office in the back.

Sakura shook her head and tried to forget about what her boss said. She can’t worry about that right now; she needs to focus on her work. Plus, she’s only got an hour left, and hopefully, Leon won’t arrive early. She went back to her duties and helped some kids who just received their new Pokémon for the Gym Challenge. That hour soared by, though, and her boss reminded her that her shift was over. “You two have fun now. Don’t you dare think about work while on your time off!” Nancy shouted from her office, giving Sakura a thumbs up. Sakura waved goodbye and flashed a smile in return as she grabbed her bag and headed out the front doors.

Low and behold, there was Leon, leaning against the shrubbery with Charizard entertaining some children by his side. He looked a bit…agitated? He hadn’t noticed her yet and seemed to have something on his mind bothering him. “Uhh, hi, Leon! Are you doing ok?” He turned towards her, and that worried appearance got masked by his usual happy self. “Of course, Sakura! Why wouldn’t I be? We’re going to have a bloody good time today and tomorrow!” Sakura still felt something was off about him, but figured that if he didn’t want to discuss it, then it’s best to let it lie. She smiled at him and spoke, “I bet we will! But first, let me get Midnight, and we’ll head to the station.” “Ah, let me join you. It’s better than just standing here waiting.” Leon faced the children still playing with Charizard and stated that they had to head out. They were sad to lose their new playmate, but listened and said their goodbyes.

After fetching Midnight from the house and collecting her suitcase packed with the necessities, they headed out together towards Wedgehurst Station. Leon put Charizard in his Poké Ball since he’s too large to have on the train. Leon scanned both their tickets through the gates, and they both hopped aboard. Little did Sakura know, however, that they were also riding first class in the dining cart. Everything was decorated beautifully from the cherry wood veneer to the Dubwool fabric chairs with Eldegoss woven blankets for warmth. If this didn’t scream luxury, she didn’t know what did. Midnight immediately jumped into the coupé, the host directed for their seating, taking the chair next to the window and announcing her approval. Leon chuckled at this display and sat across from the empty seat, where Sakura presumed, she would sit.

“So, what do you think?” Leon challenge with a devilish grin, visibly enjoying her reaction to this surprise. “I…I don’t know what to say…” she stated as she took her seat. It felt so plush and velvety with the blanket behind her, she thought it would engulf her frame. “A part of me wants to scold you for getting such expensive seating, but this all just feels too lovely right now. However, you will get an earful later!” Leon snickered at her retort. “I bet I will. Either way, I know you haven’t had dinner yet, so order whatever you want on the menu, my treat!” He picked up the menu perfectly centered before him and glanced over his options. “N-No Leon! I couldn’t! Let me at least pay for myself.” She regretted saying that after looking at the prices of the menu items. Alolan-styled Slowpoke tail for 4,000, smoked and cured Basculin for 6,000, and the Shuckle-fermented wine was 700?! She had only brought 3,000 from her savings with her, and one dessert and drink would be enough to wring her dry. She sheepishly looked up from her menu, hiding her burning cheeks as Leon gave a knowing, innocent smile.

“Something wrong with the prices, Sakura?” She glared at his playful smile. “You did this on purpose.” He faked a hurt expression and exclaimed, “How could you claim that your oldest best friend would purposely choose expensive fine dining, to treat their friend they haven’t had time to spend within so long, without her needing to pay for a single thing? Because you are completely accurate about that.” Before Sakura could make any more protests, their stewardess appeared by their table, welcome them politely, and asking for their orders. “U-Uh, give me a moment, p-please ma’am.” Sakura stuttered, speedily scanning the menu for something she might like. Leon only asked for the special, which happened to be the Basculin and some water. “Umm, can I have the seared rib-eye Tauros with a side of…Fancy Apples, and some water as well, please? Oh! And do you have Pokémon food? Something for Midnight would be great, please.” The stewardess nodded and wrote down her order before giving her a Pokémon menu.

“We currently service a variety of curries, notably Large Leeks, Fancy Apples, Boiled Eggs, and Fruit Bunch. However, we did also import some Poké Puffs from the Kalos region, if your darling is looking to try something new.” Midnight shoved her face against the menu, eagerly figuring out what to get. “Umbre-Umbre!” She pointed her paw at every fancy Poké Puff on the menu. “No, no Midnight, you are not making Leon spend that much money! She’ll have three Deluxe Spice Poké Puffs, please.” Midnight pouted and gave a vocal objection, but Sakura stroked her head. “I swear you have the stomach of a Munchlax sometimes!” Midnight begrudgingly accepted the affection and went back to staring out the window at the approaching Wilds Area. “Excellent choices. Your meals will be out shortly. If you need anything, please don’t hesitate to ask.” With a short bow, she left the table and went through one of the carriage doors.

“Your earful has doubled, Leon.” Sakura griped before continuing, “However, thank you very much for all of this. It really means a lot to me. B-But you didn’t need to go this overboard! Seeing you live in a battle is more than enough for me to be content.” Leon's mouth turned up in an endearing smile. “I just wanted to see you happy. You’ve been cooped up in your routine life for at least two years. You should get out and see the world! You do want to be a professor, and the best experience is physical!” Sakura frowned and crossed her arms. “Well, you’re the lucky one, Leon. You were given funding to go on your excursions.”

She didn’t mean for what she said to sound as cold as it appeared. Since she was never endorsed to do the Gym Challenge, she had to work vigorously and save up for a place of her own and then another for a research lab. No one wanted to endorse a professor wannabe when they had Sonia, the expected-to-be. It did make her feel a bit depressed from time to time to see how lucky those two had started, but she appreciated the solid work she put in at the Pokémon Center to achieve her dreams. She’d get to Sonia’s level eventually, even if it took a while.

The carriage doors had opened, and stewards and stewardess marched out with carts full of steaming and mouth-watering food. Sakura got distracted for a moment at all the scrumptious-looking meals heading their way, her stomach grumbling in anticipation. Midnight was jumping in her seat with glee as she excitedly waited for their food to reach them. Leon waited to reply to her remark once the food had been set down.

“Well, I hope that a trip to Wyndon Stadium will help you feel a bit closer to your dreams.” Another flash of a grin, and then he began digging into his Basculin. Sakura felt a bit guilty for her earlier words but then puzzled by his response. It seems odd but purposeful. He sure had been acting rather peculiar today. She felt she could try and get the truth out of him after dinner. For now, she’ll enjoy the exquisite food before her and feel contented being around old friends again.

**Notes for the Chapter:**

> Man inspiration has struck me hard this week. Luckily, people are liking it, so it really motivates me to keep pushing them out! Thank you everyone for all the kudos, bookmarks, and comments!


	4. A Champion’s Surprise

“What do you mean that I’ll be closer to my dreams, Leon?” Crap. He regretted the words when they came out of his stupid mouth. He had to think swiftly; otherwise, she might catch on to the surprise he had for her. Sakura may be oblivious to romance, but she is far from ignorant. They had finished their fabulous meal, Midnight laying across her lap in a food coma. “Well, what I mean by that is you’ll be able to study the battles live and interact with everyone’s Pokémon! It might help with your research.” He reasoned, proud of his save. It seemed to work too, as her raised eyebrow lowered in acceptance.

“I suppose that’s true. But I can’t just go up to the gym leaders and ask to study there Pokémon. That would be awkward.” “I’m sure they’ll be fine with it. Fans have asked for much worse.” That gave Sakura a little giggle as she finished off her water. “Anyway,” Leon began, taking the opportunity to change topics. “we’ll need to get off at Hulbury Station to switch to the nighttime train. Since they operate 24/7, they’ll be kicking us off the daytime ones.”

“What’s the difference between them? I’ve never ridden at night before.” Sakura queried, leaning back against the blanket. “Well, they don’t have dining carts; that’s for sure. It’s the same seating as before, booths and seats for everyone to sit in. However, there are a couple carriages that have small private rooms for people to sleep in. I booked one of those for us.” Both of their faces got a hint of redness at his finished statement, Sakura’s more than Leon’s. “I-I see, well, I won’t be needing to sleep for sure!” Sakura declared, obviously trying to hide a yawn that wanted to be free. He found it adorable and decided not to call her out on her bluff.

Soon Hulbury Station came upon them, and they worked to get ready to leave. Sakura shook Midnight awake and rose up from her chair, her legs feeling wobbly after relaxing for so long. Her face revealed longing as though sad to wish such a comfortable chair goodbye. Leon chuckled internally at this and reached for her suitcase while she was occupied with her thoughts. “Hey! I can carry that!” She protested, trying to snatch it out of his grasp. He swerved it expertly out her range, using his height to his advantage. “I would be a terrible host if I didn’t carry a lady’s luggage for her.” That blush from earlier came back with a vengeance on Sakura's cheeks, and she hastily looked away. “O-Oh hush. Just let me feel bad about you carrying my stuff.” They moseyed along down the aisle towards the door. “Well, you could carry Midnight if you want to hold something so badly.” He jested, earning a glare from her. Shockingly though, she did pick Midnight up, confusing the Pokémon, and carried her the rest of the way off the train.

“If your arms get tired from holding Midnight, let me know, and I’ll carry her too.” He joked and laughed as Sakura hurried past him, heading towards the chairs in the lobby. Leon sauntered behind her, sitting down beside her when she chose a decent spot. “Train shouldn’t take too long to show up. Thankfully, we should arrive at nine, so three hours left.” He spoke as he looked down at his Rotom Phone. Sakura hummed in acknowledgment and hugged Midnight closer to her. “Is the lobby too cold for you?” Leon asked, putting the suitcase on the floor. “No, I’m fine. I have Midnight to keep me warm.” Leon didn’t take the excuse for an answer and started to remove his cape. Sakura noticed his action and quickly added, “No, no, no! Then you’ll get cold! I’ll be fine! You said the train won’t take long anyw-” She was silenced by a flying cape landing on her head. “I won’t get cold, Sakura. I’m wearing shorts, leggings, and a t-shirt. And no complaints!” He grinned at her as she freed her head from underneath and begrudgingly allowed this to happen. She draped it over her body, keeping Midnight underneath it, and wrapped it across her shoulders.

“You don’t need to look out for me, Leon. A little chilliness won’t kill me. But, thank you for letting me borrow your cape.” “Of course, I’ll look out for you! You’re my best friend, and I care about you. Plus, I’m the oldest, so it’s my job too.” He bragged, earning another hilarious reaction of Sakura pouting and quietly shouting, “Only by three months!”. He gave a hearty laugh and pat her head like an innocent child. “Then you’re admitting I’m supposed to take care of you.” Another scowl from her, but she hid her face with his cape. At least, except her eyes. Was she blushing? It was a shame he wasn’t allowed to see it, but ruffled her hair instead and faced forward, letting her pull herself together.

About ten minutes of silence went by as the night train had finally pulled up. Leon stood up from his seat, already lifting the suitcase up when he glanced over and saw Sakura had dozed off a bit. He guessed she was tired from the excellent food and long day of work. He placed his hand on her shoulder and gently shook her awake. “Hey, sleepyhead, our train is here. You can sleep in one of the beds they provide.” She jolted up once she realized she had fallen asleep, causing Midnight and the cape to fall from her lap. “I-I wasn’t asleep! I was just resting my eyes!” “Heh, sure, Sakura.” She hurriedly picked up Midnight with the cape wrapped around her and followed Leon onto the train.

The room was small, but cozy in its own way. Two beds hung from opposite walls with a window in between them on the back wall, which Leon hoped will show the setting sun on their venture. No hills or mountains should try to block it. He put Sakura’s suitcase underneath the bed he assumed she would take and sat across on the other bed. “Perfect, now you have a place to rest if you’re feeling tired.” He teased as she placed Midnight down and sat on the plush mattress. “I will force myself to stay awake if I have to! Or you should keep me awake.” Sakura suddenly blushed after her statement and looked out the window, avoiding his gaze. Leon didn’t comprehend why for a moment until he took the phrase the wrong way as well. A blush crept up onto his face, and he followed suit, staring out the window.

He didn’t grasp that this was the first time in years they had been in a bedroom together; at least something close to one. They had sleepovers all the time when they were young, Sakura, Sonia, and himself; but that was before him, and Sonia went on their Gym Challenge. Ever since, they never went into each other’s rooms at home, fearful of invading one another’s privacy. Plus, then she’d see his cap collection, which he was equally as proud and embarrassed about. Maybe he could lighten the mood with something funny?

“Uh, hey. I saw something funny that Raihan sent me today, do you want to see it? It’s a video.” He was already pulling out his Rotom Phone, searching for the video in the group chat before she responded. Luckily, she agreed and leaned forward to see. “Ah, uh, it’ll be easier to sit next to you to show it, if that’s alright?” “Uh…yeah, it’s fine.” She spoke softly, barely above a whisper. He slowly stood up and took the spot next to her, making sure to leave a gap between them. The Rotom Phone floated in front of them with the video ready to play. “You can play the video now, Rotom.” The phone buzzed back in response and played the video.

“Hey, weather-enthusiasts! Check out how good of a sandstorm my Gigalith can make with his ability Sand Stream!” Raihan spoke to the camera as it floated over to show his Gigalith. Activating his ability, it put on a good sandstorm, so good you couldn’t see the Pokémon anymore. After a couple seconds passed by, the sandstorm faded, and the camera faced Raihan again. “See if you guys can beat that-ah!” Raihan’s Sandaconda burst out from under the ground and tackled its trainer, knocking him off balance and tumbling to the ground, abruptly ending the recording.

The duo burst out in laughter at Raihan’s misfortune, more so Leon since he knew the guy. But seeing Sakura in a giggle fit and calming down made him feel better. He continued this trend of showing her funny videos he found on the internet to pass the time by. He did notice her scooching closer to him to view the content until they were eventually leaning against the wall with her head resting on his shoulder. She didn’t seem to either notice or mind, but he enjoyed their position considerably. He missed being able to be this close to someone; other than Hop, of course. Just relaxing and enjoying each other’s company.

“So, what do you want to watch next?” Leon questioned, but got no response from her. Carefully turning his head, he confirmed his theory that she had fallen asleep during the last video compilation. Midnight had passed out as well on their collective laps, still bundled up in Leon’s cape. He motioned for the Rotom Phone to come closer and checked the time. It was 8:30, so there were thirty minutes before they arrive at Wyndon. He deemed he wouldn’t disturb their slumber and slowly put on his headphones to listen to more videos quietly. Yeah, he longed for this tranquility, they both needed it.

Those thirty minutes flew right on by, though, thanks to the video watching. The trained had made its stop at the Wyndon Station, and he could hear late-night passengers leaving the cart. Gloomy that the moment was over, he shook Sakura awake a second time today. She stirred awake and lifted her head up from his shoulder. “Welcome back from dreamland. I knew these beds would come into use.” Sakura’s cheeks became the reddest he had seen all day as she leaped back from being so near him. “I-I-I’m sorry I fell asleep on you! Arceus, I hope I didn’t snore or make your shoulder fall asleep!” She stammered, hastily sliding off the bed, taking Midnight with her. “You’re fine Sakura, you caused no harm, so don’t be so apologetic.” He paused for a moment, noting that she was trying to carry her suitcase. “Hey, hey, hey, we talked about this. Who’s supposed to be carrying your suitcase?” He slid off the bed as well and put his hands on his hips. “Me, because it’s my stuff, and you’ve carried it all day.” A sneaky grin grew on her face. “If you want, you can carry Midnight if you want to hold something so badly.” She repeated from earlier, opening the door and slipping out before he could retort. He sighed and looked down at Midnight, who glanced back up in confusion.

“Well, she beat me at my own game. I’ll get it later in the monorail.” He directed at Midnight, who cooed back at him. He put his cape back on around his shoulders and scooped up Midnight into his arms. He trusted Sakura didn’t wander too far from the train since he’s terrible with directions. Fortunately, she was waiting immediately outside the gate, nervously scanning the area for him. “I’m right here, but you really shouldn’t run off like that in a place you don’t know. Then again, I forget how to navigate this place even though I live here half the time.” “I know, I’m sorry. Dumb mistake on my part. But where are we heading to now?” Leon glanced around for a directional sign that pointed to the monorail system that should guide them directly to Rose of the Rondelands hotel. Locating the sign, he ushered them to head upstairs and select the hotel as the destination. Sakura was having a bit of trouble carrying her luggage up the stairs though, so Leon took this opening to switch carries and take the harder task.

The monorail was a tight squeeze for two, causing Sakura to be pressed up against Leon’s chest so the suitcase would fit. Leon became acutely aware of where his hands should be, forcing them to stay at his side to minimize her discomfort. Thankfully, the ride was brief, and they ended up at the hotel in one piece. “Oh my gosh, …it’s so huge compared to anything I’ve seen back at home.” She admired the building’s beauty for a moment before they both headed inside. After being greeted by the doorman, they stepped up to the front desk, and Leon gave Sakura back her suitcase.

“Welcome to Rose of the Rondelands. Do you have reservations with us?” The front desk man asked as protocol. “Yes, I do, it should be under Leon. Here are my tickets.” He dug around in his bag for the two hotel tickets and provided them for the man. He looked them over and checked on his computer. “Ah yes, a studio room for two nights, already paid for.” Leon grew dumbfounded by his response. “Wait, but I ordered two separate rooms for each of us.” The man paused a moment, clicking about on his computer, and then replied, “Yes, you did. But the order was changed at 6:30pm to be a studio. When the clerk asked for who names made the change, they were given Nessa and Raihan.” Those two blokes did this? They must’ve done it on purpose to tease him, but that’ll trouble Sakura for sure. “Well, is there any way to change it back?” “I’m afraid not, sir. All other rooms are booked. I hope this is not a problem for you two.” Leon looked back at Sakura, who nervously shrugged, also believing there wasn’t much they could do. “Alright, that’ll be fine then. Thanks, mate.” He nodded back at Leon and gave him two room keycards. He swore to Arceus that this better not ruin Sakura’s stay here. He still needed to convince her to join the Gym Challenge.

**Notes for the Chapter:**

> Yay another chapter for you all! A longer one too! Finished this really late at night with an early morning wake up soon to follow. I hope you guys like this chapter too!


	5. A Professor’s Dilemma

Sharing a room? With Leon? Sakura turned away from Leon as they entered the elevator, attempting to hide the flush creeping up on her cheeks. Oh, what’ll they do? May it’ll have two beds? But it’s a studio, soo it probably has only one. Heck, will they share a bed? No, she’ll take a couch, if there is one, or the floor. She wouldn’t want to-

“Hey, I’m really sorry about this, Sakura.” Leon started, his voice startling her from her thoughts. “I didn’t expect my friends to do this to me. I hope it won’t ruin your first time to Wyndon.” His voice was somber at the end, his head tilted shamefully away from her gaze. “No! Leon, don’t feel bad! Everything will be fine. My stay hasn’t been ruined just because we’ll share a room together.” The elevator made a little _ding_ , signifying that they had arrived on their floor. “Are you sure?” Leon questioned as he stepped out of the opening doors. “Absolutely!” She gave him the best confident smile she could muster for him, which still oozed with nervousness. It seemed successful, though, since she gained a smile back from him, albeit small. 

Together they sauntered down the hall to their room. Sakura admired the hallway on their way, appreciating the beautiful paintings lining the walkway and cleanest white carpet she had ever seen. “This place is certainly prideful of its luxurious appearance.” She muttered under her breath. She didn’t know if Leon caught what she said, but he did not respond. Stopping at their door, Leon pushed the keycard in and waited for the green light to flash before creaking it open and letting Sakura inside first.

Sakura didn’t expect the room to be so luxurious and modern since the exterior of the building and lobby were more rustic and historic. The living room was bathed in gold colors, from velvet couches to the drapes over the windows, and the glistening chandelier that hung above. The dining table was a dark oak that contrasted with the light colors around it brilliantly; as well as being placed in the center with windows curving around it, for the best views while eating. The kitchen to the left of the doorway genuinely showed the modern aesthetic of the open-concept room, with shiny and sleek appliances, and even a stove for cooking.

“Oh my gosh, I feel so awestruck and yet out of place in this room.” Sakura finally spoke after breaking from the trance the room had on her. Midnight had already bolted into the room and inspected every nook and cranny she could squeeze herself into. Leon stepped past her, locking the door behind them, and shuffled to the bedroom to put her stuff down. “You’ll get used to it. Also, thank Arceus, they brought my stuff up from the previous room. I left the key with them so I wouldn’t lose it on my way to and from Postwick.” She noticed him move his own suitcase out of the room and next to the couch, where he collapsed down on it in exhaustion. “W-Wait, shouldn’t you get the bedroom? Your friends did mess with you; after all, you should get the bed!” Sakura announced, stepping closer to the couch. “Nu-uh, you aren’t going to worm your way into getting less than you deserve.” Sakura blushed at his comment, but luckily his eyes were closed so he couldn’t see it. “I am getting the couch because you are my guest, and this is an inconvenience for you, not me. Besides, these couches are super comfy. So, no more arguing and go to sleep. We have a big day tomorrow.” He pulled the fluffy throw blanket off the sofa and tossed it on himself and reached for the nearest couch pillow to crash on.

She still didn’t like the idea of him sleeping on the couch. What if he got sore, and that affected his battle tomorrow? She wouldn’t be able to live with herself if her best friend lost his title in an exhibition match because of inadequate sleep. If only she wasn’t so nervous about allowing them to sleep in the same bed. It’s not like anything would happen, but she was unable to just command him to share a bed because of how embarrassed she’d be. Maybe if she just treated it as when they were young? Sometimes he, her, and Sonia would share Sakura’s bed when they had sleepovers. It wasn’t awkward then, so why did it have to be now? Ugh, curse her adult mind. After about three minutes of still being unmoved from her spot, Leon looked up from the couch and questioned, “Hey, are you alright? You don’t need to worry about-” “Leon, come sleep with me instead of on the couch!” Sakura blurted out before even thinking.

She covered her glowing cheeks with her hands and turned away from Leon. She assumed she must’ve sounded so stupid at that moment and couldn’t believe she just said those words. Little did she know, Leon was just as flushed as she was. “Y-You don’t need to say that, Sakura. I really am fine sleeping on this couch.” Well, no point in going back now on her words. “N-No! I wouldn’t be able to forgive myself i-if you lost tomorrow’s battle because of poor sleep. N-No excuses!” She fled into the bedroom and quickly unzipped her suitcase, taking out a pair of pajamas and darted into the bathroom, locking the door behind her.

My Arceus, she did it. Even if she ran away at the end, she said it! Her confidence level increased by one, till it crashed down to negative one when she realized that they would be sharing a bed together. Heck. Then again, it was a queen-size bed, and she could put Midnight between them. Yeah, she figured she could do that to make it more bearable. She slipped out of her travel clothes from today into Eevee evolution themed pajamas. She wished that Leon wouldn’t view them as childish, because they were so very comfy. Checking herself in the mirror one last time, making sure the redness entirely disappeared from her face, she unlocked the door and quietly opened it, in case Leon was sleeping.

He was, in fact, not sleeping and was facing the bathroom door while sitting on the bed. Leon looked up from his Rotom Phone and stared at her outfit. A wave of self-consciousness washed over her, and she swiftly spoke out, “T-The bathroom is ready for you to use. I-I’m sorry I took so long.” They both knew she didn’t take very long. Trying to disregard the awkwardness she felt, she scrambled around to the other edge of the bed and ducked under the covers, hiding from him. He didn’t say anything in response, which puzzled her a bit, but she felt him get up from the bed and gather his clothes to change in the bathroom. She started to feel guilty when she didn’t hear the click of a locked door. He trusted her enough to not walk in on her, yet she couldn’t offer the same. Gosh, she was just making this night worse and worse.

Luckily, Midnight sensed her owner’s distress and hopped onto the bed, laying down beside her and placing her paw on Sakura’s forehead. Midnight then began to make her yellow rings glow bright, growling at her head. It was a gesture Sakura found adorable and oddly comforting, since when an Umbreon’s rings glow it’s supposed to scare anyone nearby. But Sakura knew Midnight wasn’t trying to scare her, only her thoughts. She gave her a praising pat on the head for a job well done and hugged her close.

Once she heard the door open to the bathroom, she looked up at Leon and suddenly felt better about her attire choice. He was wearing just a t-shirt and sweatpants, but they were both Charizard themed. She tried to stifle a giggle, but Leon could tell she wanted to laugh. “Hey, I didn’t laugh at your PJs. Be courteous, Sakura!” He scolded, but a grin featured alongside his scolding. He got under the covers as well, keep a good two-foot distance away. Midnight took to her post of being between them since Midnight always “slept” next to Sakura every night. In reality, she just kept guard while her owner appeared vulnerable at night. “Night Sakura,” Leon mumbled, turned away from her. “Goodnight, Leon. Sleep well.” Sakura mumbled back, ready for a goodnight’s rest after such a long and entertaining day. During the night, both had shuffled in their sleep, and Midnight almost got crushed by Leon as he unconsciously sought for more warmth. Midnight had moved out of the way, and soon, Leon’s body found Sakura’s, and he snuggled in close, eventually draping an arm over her.

~~~~~~

Leon was the first to wake up, instantly discerning that he was embracing Sakura. Shit, fuck, heck, damn. Even if this was a soothing feeling, if she woke up now, he’d be toast. At the same time, he sensed some tense energy from the foot of the bed. Very carefully turning his head as to not wake up Sakura, he saw Midnight’s piercing gaze. Her expression was neutral, but her red eyes radiated, “ _Look at what you’ve done._ ” He knew they needed to get up, but not like this. He prayed to Arceus that Sakura was still a heavy sleeper and cautiously removed his arm from under her. She stirred a little, which made his heart jump twenty feet in the air, but thankfully she didn’t awaken. After he freed his arm, he slowly lifted the other off her waist and scooched back to his side of the bed. Giving a sigh of relief, he looked back at Midnight, who gave him another stare down before curling back up at her original spot. Hopefully, Midnight won’t rat him out to Sakura, but at least she wouldn’t wake up with embarrassment first thing in the morning. Leon did feel a bit disappointed, though, that it couldn’t have lasted longer. He couldn’t remember how long ago it was when he had someone that wasn’t a Pokémon to curl up with.

~~~~~~

“Saaaakuuuraaaa, it’s time to get up.” That was all the warning she had before Midnight was tossed right beside her face. It startled her awake so bad, she almost fell out of bed. Keyword almost, since Leon’s Aegislash floated bedside the mattress, preventing her from falling off. “Freaking Arceus, Leon! You didn’t need to wake me up that way!” She shouted, catching her breath. “Don’t blame me, Midnight wanted to do it.” Her mischievous partner gave her a proud, smuggest grin, hopping off the bed and heading out the room. “Oh, and I’ve already ordered us some breakfast, should be arriving soon. Might want to get dressed if you don’t want anyone else to see your cu- err…pajamas.” He was already dressed in his usual attire, hair fixed, and refreshed before breakfast even came. Sakura could only guess he let her sleep in since he looked ready to head out the door. 

“Yeah, you’re right. It’s bad enough you saw me wearing them.” Leon frowned at her self-demining comment. “They look fine on you. As fine as my Charizard ones look on me. It’s not like either of us expected anyone to see them.” She nodded in agreement and got out of bed. Gathering her toiletries and a new outfit to wear today, she headed to the restroom and didn’t lock the door. It was a little nerve-wracking not to, but she wanted to prove to herself that she could trust Leon. Plus, it wouldn’t take long to get dressed anyway, just some light blue jeans and a long-sleeve, gray blouse. She knew it might get chilly today, so she decided to dress cozy.

In the middle of brushing her lengthy, brunette hair, she overheard the faint sounds of a door opening and something being rolled in with metal clanking. She assumed the food had arrived and finished up removing the last tangles, heading out towards the kitchen. Leon had already laid out the food for them to eat, Midnight getting her own bowl of fresh, spicy curry. “The menu you here is just as extravagant as the one on the train, but they do take requests. I thought you might enjoy a break from the laps of luxury and have a simple breakfast of Grumpig bacon, Blissey eggs, and pancakes.” Leon lifted the polished metal coverings of each dish as he announced them. Sakura wouldn’t call it escaping luxury since even if they were just serving plates, they looked mathematically perfect. Leon noticed this as well and gave a sheepish chuckle. “Well, as close as one can escape. Still, it should be delicious!” Sakura giggled as he tried to salvage his attempt at decreasing such exquisiteness. “It’s fine, Leon, I appreciate the effort.” She took one of the empty plates and started serving herself the portions she wanted of each, getting extra bacon and piling the syrup on the pancakes.

“It is a shame, though, that we won’t get to use the top-of-the-line cookware here.” She sat down at the opposite end of the table and began chowing down on a scrumptious breakfast. “Well, since the exhibition match doesn’t start till 2pm, how about we look around the city and buy some ingredients to make lunch here?” “Yeah! That sounds like a plan!” Sakura replied eagerly, excited about the aspect of exploring a new place, and creating homecooked food. Leon had a beaming smile on his face as he happily munched down on his breakfast.

**Notes for the Chapter:**

> I'm sorry this took so long to publish out. I've had a lot happening since the last update from finals for classes to my emotional support pet having kidney failure. It's been very rough. However, I made this chapter extra long for you all, so I hope you enjoy it!
> 
> Also, some things to point out:  
> *I originally wanted to write this as an x reader story, but I find it difficult to create reactions and personality out of a characters who's not suppose to have much. So, if you want, you can put yourself in place of Sakura, though it may not represent your personality as well.  
> *If people also don't like the name Sakura in general, you can just imagine a different name in case her name appears out of place in the story. It's just a name I really like and so I put it on this character.


	6. A Champion’s Intrusion

Leon was very grateful that Sakura was relishing her first visit to Wyndon; what with the hiccup they had last night. Though, another issue came to light as they consumed their breakfast; how is Leon going to show her Wyndon with how lousy he is at directions? He could have his buddy, Charizard, out to guide the way, but that’ll encourage people to bother them since there will be more tourists mingling around the city. He could locate a map of Wyndon. Maybe the lobby might have some? There would be only one opportunity to get it so that Sakura isn't left alone in a strange place. It’s decided then.

“Hey, I’m going down to the lobby to get something. I’ll be back really quick. Is there anything you’d like while I’m down there?” Leon questioned, standing up from his chair and heading to the bedroom to search for a different cap than his usual one. Choosing a half black and orange one, he straightened it on his head and heard Sakura reply, “No, I’m good. I’m not sure what I’d need from there anyway.” A pause passed, and right when Leon was about to step out the door, she interjected, “Oh! A map would be good, actually! If they have them down there, that is. That way, we won’t get lost!” Leon sighed internally; she knew him too well. But, it’s what he was going to get anyway. “Gotcha. I’ll be back shortly.” Closing the door, he strode down the hallway to the elevators.

Once the elevator doors opened to the lobby, there was an unexpected, familiar face just about to enter himself. “Oh sup, Leon! I was just about to head your way.” Raihan greeted, stepping aside to let Leon pass. “Hey Raihan, why did you want to meet me in my room? You’re going to see me later today.” Leon shuffled by Raihan and moved toward the front desk. Leon felt a bit uneasy by this out-of-character appearance of his rival. Usually, Raihan would greet him at the stadium, and they’d chat about how they’ll pummel each other into the ground. Raihan followed him, arms crossed behind his head, and answered, “What, I can’t see my rival when we’re in the same town? You live here, after all. Besides, I wouldn’t mind meeting your friend before the match occurred.” Leon tensed at that last statement. He knew how Raihan was with women, how he acted around them. It didn’t really bother Leon much, since it usually wasn’t someone he knew, and Raihan wasn’t rude or obnoxious, but he was an extreme flirt, especially if someone piqued his interest. Though, maybe Sakura wouldn’t be his type. He never saw Raihan show flirtatious interest towards shy fans, at least, at the stadium.

“Well, I suppose you can meet her now. We were about to leave to explore the city.” He found a small stand with pamphlet maps stocked and took two of them. “She’s never been here before.” Leon went back to the elevators, Raihan tailing behind. “Oh, really? Well, we’ll have to show her how great this place is.” Raihan chimed in. Leon hid his confused grimace from Raihan. We? Who said he could just tag along? Why is Raihan feeling the need to inject himself between him and Sakura? “Well, it was kind of just meant to be the two of us. We’d be catching up since I haven’t been able to see her in a long time.” Leon mumbled, still audible to Raihan, though. Raihan raised an eyebrow at him but then gave a devilish grin. “So, it’s a date then?” Leon’s cheeks flushed as he gave a menacing glower towards Raihan.

“I told you before, we’re just friends. Please stop misconstruing things.” Raihan was unfazed by his glare, grin ever-present as he stepped out of the elevator before Leon did. “Uh-huh. Just friends. Read ya loud and clear, Champion.” Leon will _enjoy_ beating him in the exhibition match later today. Raihan found delight in pushing his buttons from time to time, but this onslaught of teasing was becoming intolerable. Leon brushed past him to the front, leading the way to their studio room. Thankfully, Raihan stayed silent till Leon stopped at the door.

“You’d better not tease Sakura this way. You know what I’m trying to do, and I don’t want you making her uncomfortable or hesitant to join the Gym Challenge.” Leon spat, but the dragon tamer still wasn’t affected by his meager threat. “I’m here to help you, dude. She’ll be wanting to join immediately once she gets a load of me.” Leon pulled Raihan’s dragon beanie over his entire face after that comment and opened the door. “I’m back, Sakura. I’m sorry it took so long. One of the gym leaders decided to stop by early and say hi to us.” Leon strained to sound peppy for her since he didn’t want to concern her with his annoyance.

Raihan had already adjusted himself back to normal and waved from behind Leon. “Sup! I’m Raihan, the dragon-type specialist and weather expert.” Raihan tried to shove around Leon, but Leon caught his hood before he could get far. Sakura gave a small, nervous wave after looking up from her Rotom Phone and greeted, “H-Hello, Mr. Raihan. My name is Sakura. It’s nice to meet you.” “Oh, don’t call me mister, that’s way too formal. Just Raihan is fine.” Leon let go of Raihan after the introduction and noticed the table was free of plates. “Did the cleaning folks come up and get the dishes?” Leon asked, but Sakura shook her head. “I just cleaned them while you were away. They’re in the sink. I thought it would be a nice surprise when they arrive since then it’ll be less work to deal with.” Her kindness made Leon smile endearingly at her before Raihan got in his sights.

“So, Sakura, I heard you’re new to this city. It’s pretty large compared to Postwick? I hope it’s not overwhelming.” Raihan had stolen a seat beside her at the dining table, causing Sakura to flinch at the sudden closeness. “Y-Yeah, it’s big. B-But it’s pretty too! I can’t wait to see all the new Pokémon I haven’t discovered yet and go shopping for local goodies. I think Midnight will have fun as well.” Once her name was spoken, Midnight hopped onto Sakura’s lap and gave the neutral stare down at Raihan that she gave Leon the night before. It gave him comfort having Midnight feeling just as weary about Raihan as he was. Then again, she has always been wary of strangers ever since _that_ happened.

Leon stood behind the chair across from Raihan, watching the interaction between him and Midnight. Sakura joined him as well, observing as Raihan and Midnight stared at each other. “Is this Umbreon yours, Sakura? They’re cool Pokémon!” Midnight’s ears dipped down a tad at the abrupt volume change, and Raihan noticed. “Ah, they must not be fond of strangers.” Raihan sheepishly remarked. “I’m sorry about her. She’s a bit protective of me.” Sakura picked up Midnight and put her back on the floor. “I’ll be fine, Midnight. This is one of Leon’s friends, so I’m sure they’re nice!” Sakura gave a reassuring smile at her, but Midnight only huffed and sat beside the chair leg. “Looks like your face can’t win all the ladies.” Leon jabbed at Raihan with a smirk, causing him to get a playful glare in return. Sakura giggled quietly at the stab to Raihan's pride.

“That’s why food is always the second option.” Raihan reached into his jacket pocket and pulled out a plastic bag filled with various berries. “I found these berries in Hammerlocke Hills near the entrance to Hammerlocke. They’re very subtle in flavor, though, so pick the one you’d like.” Midnight sniffed the bag before stealing it out of his hand and running to the bedroom. Leon and Sakura both chuckled at Raihan’s loss of his berries. “Hey! I didn’t say you could have all of them!” He shouted after Midnight, who didn’t come out of the room and hunted through its contents. Raihan sighed and shrugged, “She’d better be best friends with me after snatching all my food for my Pokémon.”

“Wait, what?! No Midnight! Give them back to Raihan! It’s not nice to let other Pokémon go hungry!” Sakura leaped from her chair and rushed into the bedroom to retrieve the stolen goods. Raihan grinned deviously as he watched her leave. “Tell me you tease her like that too. She makes it too easy.” “Alright, Raihan, enough of those remarks. I think it’s time you go, now that you’ve met her. You’ll get to talk more with her later. You’ve stalled us enough from going on our tour.” Raihan cocked an eyebrow at him and stood up from his chair. “Well, why don’t we let Sakura decide if I can join on your little adventure or not?” He turned towards the bedroom door and yelled, “Sakura! Leon was telling me about the tour you’re having in the city. Mind if I tag along? I know all of the best spots to visit for first-timers.” Sakura walked out with Midnight in one arm and the bag half-empty of its berries in the other hand. “Huh? Oh! Uhm, sure, if you want to. I’m not sure if it’ll be eventful, though. The main things I wish to see are the Ferris Wheel and a store so I can make lunch here.”

Raihan gave a winning smirk towards Leon and instantly switched to a joyful smile once he faced Sakura again. “Great! Let’s head out then. You’re going to love this place, girl. There’s literally an endless supply of things to do.” Raihan rambled as he headed out the door. “O-Oh, that sounds nice! Maybe I’ll have to come back here again someday to check it all out.” Sakura grabbed her mini-backpack and unzipped the top part open a bit. Midnight stood partially inside and rested her paws on the back of Sakura’s shoulders once the backpack was on. Both Leon and Raihan gave her perplexed looks at the display. “Ah, Midnight likes to be up high sometimes if we’re in an unfamiliar place. I assume she likes to scout ahead.” Both accepted this answer as she headed out the door as well, Leon taking the rear and locking the door. “Oh, by the way, I got those maps for us. There’s one for both of us.” Leon handed Sakura a map of Wyndon. Well, it would’ve gone to Sakura, had Midnight not yanked it out of his hand.

“Gah! Midnight, why are you being so ornery today?” Sakura questioned, trying to take the map from her. Raihan stopped, pushed the elevator button, and got near Sakura to reach passed her shoulders, taking the map out of Midnight’s mouth. Midnight, of course, did not like this and jumped clumsily out from the backpack and onto Raihan’s face, sending Raihan and Sakura both tumbling. “Shit!” Leon barked as he took ahold of her arm and pulled her back before she ended up falling on top Raihan. He absolutely didn’t want to imagine that position. Raihan, however, fell into the elevator as the doors open; fortunately, or unfortunately, with no one occupying the space. He caught himself on the bar inside nonetheless, before any harm could come to him.

“Oh my god, Raihan! I’m so sorry! Are you ok? You didn’t hit your head, right?” Sakura drew free from Leon’s grasp and picked up Midnight. “Midnight, if you don’t start behaving, I’m going to leave you in the hotel room until I get back to make lunch.” Sakura scolded, frowning at her partner. “Umbre! Umbre um!” Midnight protested, snuggling Sakura’s face again to gain forgiveness. “It’s fine, Sakura, really. I’ve been tackled by way bigger Pokemon. Try a Flygon flying at full speed after winning a battle.” This just made Sakura more worried, until Leon patted her head. “He’s tougher than he looks. Otherwise, he wouldn’t be my biggest rival.” Or his greatest pain in the ass, sometimes. She seemed to take comfort in his words and relaxed a bit. 

Once everyone left the building, they collectively looked at Leon’s map because it didn’t have bite holes through it or get crumpled up in the fall. It had already become 11am, so there wasn’t much time to see big-ticket items like the Ferris Wheel or Rose Tower. Leon had offered for Sakura to see them tomorrow morning since they’d have till 4pm to view the rest of the city before the train came. Sadly, Leon knew he wouldn’t be able to relax with Raihan around. He couldn’t tell yet if Raihan was just striving to rile him up or if he had a genuine interest in Sakura. For now, though, he’d lay low and keep his cool. If Raihan's intent was to make him agitated before the match, he wouldn’t let him taste victory. 

**Notes for the Chapter:**

> Hello! I'm sorry it took so long for the next chapter to be posted again. Life has been keeping me busy. Hope you all are ready for the love triangle that was promised!  
> By the way, I have a proof reader now! So, chapter quality should improve! I also went back to previous chapters to make certain sections more clear and better quality.  
> I also might start making chapters a bit longer because of wanting story plot points in certain character's perspectives. So look forward to possibly more time between chapters, but longer chapters!


	7. A Rival’s Mission

Raihan wasn’t expecting Leon’s friend to be so goddamn entertaining. Raihan typically avoids super shy people because they appeared more focused on restraining themselves than chilling and having a good time. Sakura, however, didn’t seem as timid as Leon stated in the text messages prior. He was expecting a bit more nervousness than what she was showing since he knew Leon fancied the energetic and diffident type of people. While she was, in fact, timid, she could push past it when conversing about topics that interest her. But, because she took every phrase so literally, it made it so much more amusing to tease her here and there.

Though how long Leon would let him push the boundaries was up to him. It was incredibly apparent that his rival had protective feelings for Sakura, whether it be tied to romance or friendship was still unclear to him. He hadn’t mentioned much about her during the conversation, even before saying it to everyone. If this was a childhood friend, why would Leon never speak about her to the group? Even Nessa didn’t know jack about her, and she’s second closest to Leon—Hop being the first. The more Raihan pondered about this unheard-of relationship, the more intrigued and captivated he became.

“So, Raihan, what are those ‘best spots for first-timers’ you were talking about?” Leon quoted, breaking Raihan out from his train of thoughts. “Huh? Ah! Yes, so, clearly the Battle Café. We don’t need to eat there, but we can battle to impress the folks. A little sneak-peek for the viewers.” He winked at Sakura after the last sentence, causing her to stiffen up, and her cheeks turn a light shade of pink. Her Umbreon didn’t like that gesture, unfortunately, and policed him by smacking his head. The abuse given to him made Sakura and Leon giggle in response. What is with that Pokémon? He’s never seen such a shielding ‘mon before, even those around little kids. “I think we can wait on the battling till the match. I know you’re itching to lose again Raihan, but lets at least keep your pride intact till then.” Leon teased, causing a slight twinge of anger to appear on Raihan’s face before quelling it down with a mocking reply. “Oh, I think you’re actually stalling because you’re afraid of losing your perfect record of wins. Wouldn’t want Sakura’s first live match to be a loss on your end, right?” That earned a low growl from Leon, but both got their debacle interrupted by Sakura taking the map and stepping between them.

“P-Please don’t fight you two! W-We’re supposed to be having a fun and relaxing time exploring the city! How about we go to the Battle Café to see what it’s like, and then we figure out where to go from there? Does that sound fair?” A peacekeeper, huh? That was also unexpected. Albeit, Sakura stuttered the words out, but getting between the two strongest Pokémon Trainers in the region still takes balls to accomplish. “I’m sorry, Sakura. I don’t want to make this an unenjoyable experience for you. If you want to go to the Battle Café, then I’ll happily follow.” Leon apologized, shamefully looking away from her gaze. Raihan crossed his arms and sighed. “I’m sorry too, I guess. Let’s head over.” Sakura beamed up at both of them and went back to her map, leading the way to the Battle Café.

Maybe he should be a bit more careful with his jabs at Leon. She didn’t defend either of them, though, so as long as his teases are low tier, then that shouldn’t affect her enjoyment. Suddenly, Raihan had a brilliant idea after realizing where they were headed. He tugged Leon farther back from Sakura, earning a menacing glare and an annoyed “What?” from him. “Hey, I’ve got a great idea.” Raihan began, whispering, “What if we let Sakura battle at the café? I want to see how strong that Umbreon of hers is, and it’s secretly testing her to see if she’s worthy of joining the Gym Challenge. I’d say that’s a win-win for both of us.” Raihan released Leon’s arm and gave him a moment to think it over. “Alright fine, but only if she wants to. Don’t force her to do it.” Leon grumbled, picking up the pace to meet Sakuras. Raihan grinned when Leon agreed with him and went past him, keeping stride next to Sakura. He was determined to get some more information about who she was, so the best time to ask when they’re heading to and from places.

“So, Sakura, how long have you known Leon?” Both she and her Umbreon glanced at him. Sakura in innocent confusion and her Pokémon with an “I’m ready to swat you away again” look. “Oh, uh, I’m just curious. I’ve known Leon for many years that I didn’t know there was someone else who knew him longer besides Sonia.” Raihan noticed a slight downcast of her eyes, but she quickly replaced it with a smile. “I’ve known him about as long as Sonia has. Maybe a bit earlier, since we were neighbors, but not by much. We all met at the same school.” “I see, was that when you got your Umbreon?” Sakura glanced from the map to him with a pause, but still answered his question, with a little skepticism in her tone. “Midnight wasn’t an Umbreon at the time, she was an Eevee. I had her before I started school.” “Dang! Growing up with a partner, Pokémon must be nice.”

Leon piped up from the back, “You didn’t grow up with a partner Pokémon?” Raihan shook his head and shrugged. “I was too interested in the weather to care about Pokémon at first. Then my dad said I had to join the Gym Challenge because I didn’t do it last year when every ten-year-old around the block had. He got me endorsed by Macro Cosmos Bank, where he worked and gave me a female Axew. I don’t own that Pokémon anymore, it wasn’t helpful for my fighting style, so Leon has it now.” In his ramblings, he didn’t realize that they had arrived at their destination, or that Leon and Sakura were staring at him intently.

“You gave me your first Pokémon?!” Leon shouted, hands atop his cap in shock, and jaw dropped. Raihan raised an eyebrow at his confusion. Did he forget to tell him it was? “Well, yeah. You’re second in being able to tame dragon types, who else would I give her too? Besides, she seems happy in your care, so I clearly made the right choice.” While Leon processed the sudden news to him, Sakura had interjected her inquires as well. “What was your first team like? Did you get more dragon types after that? Do you think you could let me see your technique in bonding with dragon types?” Wow, that’s a lot of questions. He believed he must’ve hit a topic of interest. Raihan grinned internally at the opportunity to pull another tease. Wrapping his arm around Sakura’s shoulders, he responded in a cheery tone. “Sure, I can show you some techniques later, just come over tonight, and I’ll introduce ya to the team!”

Her eyes seem to light up with innocent eagerness, not even taking the wording in an impure way. Leon, however, was not one to disappoint. Upon hearing the words, he snapped back into reality and shot, “Excuse me, what? No, no, no. That’s not a good idea.” Raihan had to suppress bawling out laughing at how pissed Leon looked. “Huh? Why isn’t it a good idea, Leon?” Sakura queried, still unaware of Raihan’s arm around her. Leon hesitated for a moment, searching for the right way to answer her question. “Because…we’re busy tonight! There’s the Gym Leader Banquet tonight, so Raihan will be busy and probably feel tired afterward, right, Raihan?” Leon spat his name out with a hidden intensity in his amber eyes. It was a joke after all, so Raihan played along, somewhat. “Oh shit, you’re right, I forgot. Maybe some other time. If you ever end up in Hammerlocke, I’ll give you an up-close and personal experience with them.” He grinned and removed his arm from her. “Anyway, come on, let’s show you the fun of a Battle Café.”

Raihan opened the door and let Sakura in first, Leon follow closely behind and tossing a scowl his way. “Ohhh, man! It’s so cozy in here!” Sakura announced, taking in all the décor. There was a combination of diamond tile and wood floors, the wood being around the table areas while the tile making pathways to the counter and sitting bar. Medium-sized plush blankets were folded and beside each table, supposedly for Pokémon of the size to rest on while their Trainers ate. The chairs and barstools were wooden as well with a red-apple finish that complimented the darker garnet counter. It’s a shame she won’t be able to appreciate the cozy atmosphere for long.

Everyone headed to the counter and were greeted by the Café Master, Richard. “Welcome to the Battle Café, folks! My name is Richard. What can I get for ya today?” Raihan pushed to the front and proudly stated, “Two fruit coolers and one battle, please!” “W-Wait, a battle? Do we have time for that?” Sakura stuttered but was ignored. “Alright, coming right up. Which one of you am I battling? If you win, you’ll get a free treat on the house!” Raihan jotted his thumb beside him at Sakura. “This little lady right here. It’s her first time at one of these, so go easy on her.” Richard nodded and gave a big grin. “Sounds good, I’ll prepare your drinks for you before the battle starts. Be ready and outside in ten minutes.” Richard left the counter and went into the back kitchen before Sakura could object.

Sakura grabbed both his and Leon’s wrists and dragged them outside, looking like she was ready to give an earful. Once they were back outside, she let them free and crossed her arms over her chest. “Why am I battling? I’m not good at fighting! I’m no Trainer! You guys should be the ones battling if you wanted to show off this feature.” “The best way to experience Wyndon is to get right in the middle of it. It’s waaaay better than just watching from afar, which you’ll be doing later today anyway. C’mon Sakura, show us what you and your Umbreon are made of!” Raihan encouraged, giving her a double thumbs-up. Unable to persuade Raihan to call off the match, she looked towards Leon for aid. There would be none for him to give, though, other than more convincing support.

“I think you’ll do great, Sakura. I’ve seen you battle in the past. You and Midnight are a powerful pair thanks to the bond you two have formed.” Leon put a reassuring hand on her shoulder. “Just try it. Who knows, it might be fun!” With a kind, million-dollar smile, it was hook, line, and sinker for Sakura. The bond between those two must also be solid for Sakura to instantly give in like that, or Leon just had a way with words. Raihan didn’t know, and probably wouldn’t find out until he gathered more details about Sakura’s past with Leon.

Right at the dot of ten minutes, the Café Master came out with the two drinks they ordered in hand and offered them to him and Leon. “There you go sirs, two fruit coolers.” Both thanked him as he headed to be parallel with the right side of the café, Sakura following his lead, but on the opposite side. “This is a double battle lassie; do you have two Pokémon?” Shit, he forgot about that. “No, I only have my Umbreon with me, can we do a single battle instead?” Richard nodded, taking one of his Poké Balls out from his pocket. “Single battle it is. Go, Alcremie!” Wringing back his arm, he pushed the center button and threw the ball pitcher-style onto the field. A Caramel Swirl form Alcremie landed perfectly in place with a little twirl for flair. Sakura’s Umbreon shimmied out of her backpack and leaped off her shoulder, also landing with similar grace. Upon landing, she gave a low growl toward their opponent.

“Hey,” Raihan nudged at Leon as he sipped his fruity beverage, “Who do you think will win?” “Just watch, let it be a surprise. Plus, this is supposed to be an assessment, I need to focus.” Leon frustratingly whispered, keeping his eyes on the match. Hmph, guess Leon plans to keep his mouth shut. So be it. Hopefully, it’ll still be an exciting battle. That Umbreon of hers is really aggressive, so polar to her owner’s behavior. Raihan pondered on what could’ve made the Pokémon so hostile towards almost anyone who came near Sakura. Maybe an accident happened?

Raihan was pulled from his contemplation when the Umbreon started attacking without an order of attack, mercilessly targeting a liquid shot of poison at the Alcremie, directly splattering all over the Pokémon. While the Alcremie was poisoned, it tried to aim a Dazzling Gleam at its enemy, their body glowing brightly before shooting rainbow rays of light. Umbreon dodged them all with unmatched speed and agility, still with no say from Sakura. Then again, Sakura looked just as surprised as Leon and Raihan were at the spectacle. Richard commanded for his Pokémon to use Magical Leaf to gain some distance. However, while the attack still hit, the Umbreon was unfazed by it. Then she grabbed the Alcremie’s arm, flinging the helpless ‘mon into the air, all while being grasped and slamming it into the ground. The Alcremie wasn’t as hurt by this move, do to Foul Play being a Dark-type move, but the poison had made the damage taken hurt a bit more.

“Quick Alcremie, grab onto that Umbreon and use Dazzling Gleam again!” This took Sakura, and her Pokémon back as Sakura yelled, “Dodge it, Midnight! Get away!” Her Pokémon struggled to break loose, but the usually creamy form became stiffer with each pull. A straight hit into the Umbreon’s body sent it flying once the Alcremie let go and released the burst of light. It laid still on the ground for a moment before swiftly standing back on its four paws, looking way more pissed than it was before. So much so, that its yellow circles began to glow ominously, striking fear into the Alcremie. “Midnight, use Wish to heal yourself! Don’t attack yet!” The Umbreon gave an annoyed grunt at her Trainer, but did as told, closing its eyes and praying to be healed. “Alcremie, use Recover as well.”

“Don’t give it time to heal fully, Midnight! Use Foul Play!” That Umbreon’s ‘er Midnight’s probably should try to remember that name’ eyes shot wide open and it charged at its foe again. However, this time it went from behind the Alcremie and bit down on the cream around its neck, before yanking up and suplexing it to the ground. The Alcremie was getting exhausted being thrown everywhere, and the poison weakening it by the second. It was told once more to use Dazzling Gleam, but Sakura declared, “Midnight, use Protect to block that attack!” This time there was no hesitation from Midnight, and a green force field surrounded her, shielding her from the attack. During that time, Midnight’s wish had come true and became mostly healed from the damage she’d taken prior. Richard tried to have Alcremie attack again, but it had succumbed to the poison and a lack of will to go on, fainting to the ground.

Because the battlers and duo watching them were so immersed in the fight, they didn’t realize a small crowd had appeared to watch the battle. They were also in awe at the close battle with a Pokémon who was at a disadvantage from the start. The silence of the end was disturbed by clapping from Richard as he withdrew his Alcremie back into its Poké Ball. “You fought really well! I was going easy at first, but you and your Umbreon really turned the tides. I recommend trying to curb its viciousness, though, as it looks like it may not listen to you if it’s so focused on its enemy.” Richard extended his hand out, and Sakura slowly took it, giving it a firm shake. The crowd then returned to their original plans, giving “congratulations” and “good jobs” to Sakura as they left.

Sakura did not share the same awe and enthusiasm that everyone else felt. She looked as though her victory had come as the result of a gruesome slaughter. A truly odd and conflicting expression and one Raihan was not prepared for. Leon, however, was much better equipped to deal with her than he was. He was at her side in an instant, after giving Raihan the forgotten fruit cooler, and was squeezing her to death in a hug. “That was amazing, Sakura! You were incredible! You should feel so proud of yourself and Midnight!” She seemed to snap out of her stupor and hugged Leon back with a little less excitement. “Yeah, I guess I really did it.” She breathed, beginning to relax into the hug. Raihan ambled up to them, prodding, “Hey, the cup-holder guy wants in on this action!” Placing the cups on the ground, Raihan made it into a group hug and ruffled Sakura’s hair. “Nice job, kid! Midnight showed that Pokémon who’s boss!”

After Sakura was done giving loving praise to Midnight, Richard came up to the group with what appeared to be two soft-serve ice cream cones. “Here’s the treat that a promised for you, ma’am. Two Casteliacones, one for you and your Umbreon.” Whatever anxieties or surprise Sakura had felt prior became promptly nonexistent as she nearly teleported next to the man, eagerly eying the treats like a Yamper. “Can I really have these?” she asked, her gaze never leaving the ice cream. Richard laughed and handed it to her. “Of course, dear. You earned them! Have a nice time in the city, folks.” With that, Richard went back into his café.

Without even thinking, Sakura sat down on the sidewalk, back against the café wall—with Midnight immediately jumping into her lap—and both began licking the delicious dessert in one hand while lowering her other for Midnight to enjoy hers. She must really like her sweets, and so does Midnight. Both men shrugged it off as they grabbed their no longer cold fruit coolers and sat on each side of her. Raihan jokingly wondered, “Hey, you going to share with us? It was a workout just watching you battle.” “Nope.” Sakura retorted with no remorse, licking up the cone where the ice cream was melting. Raihan chuckled at the response and watched as she savored the sweet cream. Though, she was awfully slow and methodical about it. After thinking about it for a moment, the dirtier parts of his mind turned the image before him from pure joy to lewd pleasure. He shook the thoughts from his head and looked away, a blush creeping upon him.

Why the hell did he imagine that? His mind may be in the gutter a lot, but that’s just with stupid innuendos, not with full imagery. Sakura, unfortunately, noticed his frustrations and asked with a concerned look, “Are you ok, Raihan? Is something bothering you?” He hesitated to face her, worried she might catch a glimpse of his reddened face, but bit the bullet and did it anyway. Immediately he noted the ice cream dripping from the side of her lips. _‘Damn, they looked soft. Hey, hey! Stop that brain! Pull yourself together, man.’_ “Uh, yeah, you’ve got some cream on the side of your lip.” He couldn’t even realize to stop his hand before brushing his thumb against those lips, rubbing the ice cream off them. ‘ _Fuck, they were soft_.’

Sakura’s cheeks tinted pink as she stammered, “A-Ah, sorry! I should’ve grabbed some napkins from inside before chowing down on this. I didn’t mean to get your thumb sticky.” Raihan wasn’t even trying to tease her this time, but Arceus, he really needed to get his mind out of the gutter. Looking at Leon would probably help. And it did. Leon was fuming at the previous display between them; it was almost comical. Clearly now, through this mindset, he could see this wasn’t an overprotective friendship. Leon liked Sakura, but either she didn’t care or was too oblivious to recognize the signs. Poor girl if she was oblivious, because now there were two, she wouldn’t know to worry about. Well, at least not in the like department, yet, but _definitely_ in the interested department.

**Notes for the Chapter:**

> What's this? A double long chapter? Yup! As an apology for being almost a month after the next update, you guys get a longer chapter! There's been soooo much going on in my life, what with the virus, natural disasters, and finals; it's been tough to find time to write. I also thought it would be a nice twist to have the chapter in Raihan's perspective, so I hope you all enjoy that!
> 
> As always, have fun reading and feel free to comment and share your input! Always looking on ways to improve!


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